Taking Chances
by youdalwayswin
Summary: Will Schuester and Emma Pillsbury — together, they are a beautiful mess.
1. Chapter 1

**A/N**: (**This chapter has been edited**.) First of all, I would like to thank those who viewed (and will view) this fanfiction. I wrote this when I was in the eighth grade and I didn't know a lot in writing stories. So I read the negative reviews and I spent the past three years trying to improve my writing. (The characters seem out of character and the plot is crazy and random. Yes, I see that now.) I am going to finish this fic just as many of you requested. Again, thank you so much for everything. -youdalwayswin

Disclaimer: I do not own Glee.

* * *

Just when the New Directions thought that they were done for; that they would go their separate ways when they had finally seen each other as family, something unexpected happened. And it came in the form of Sue Sylvester. She talked to Principal Figgins and they were given another chance to make a comeback. Another chance to see if they could become something great and special, all of them together.

With a new school year unfolding, Will Schuester regained confidence in himself, in his kids, and in what they can do. However, there was still emptiness in the pit of his stomach — a hole in his heart — that can only be filled by one person: _Emma Pillsbury_.

Just two months ago, he finally admitted to himself and to her that he loved her. But he was left hanging for the rest of the summer since he never mustered up enough courage to drop by to talk to her again.

As he heads to his office, he smiles when he sees Rachel, Tina and Mercedes deciding on which pictures of the Glee Club to hang in their lockers. However, his smile fades when he stops a few lockers away from Emma's office. He sees her moving a bouquet of flowers to a vase and thinks that it's from Carl Howell, her new boyfriend.

"Hey, Chin [Keith] Urban," Sue whispers in his ear. Will flinches, an involuntary physical reaction to her creeping up on him no doubt. "I see you're stalking Annie."

"I'm not stalking Emma." He says shortly and he turns to her, only to flinch again when he realizes how close Sue is standing to him.

"You may not be stalking her but I know that you are absolutely bothered by that bouquet of flowers," Sue grinned. "I can smell the sweat of jealousy on you."

"I'm not jealous. I know Emma really does love me." He says to Sue and she sticks out her tongue in disgust.

"So you think that she's the Nicole Gingerbread-man to your Chin Urban? Have you ever considered that maybe she doesn't love you?" Will sighs in that infuriating way that he does when he won't accept another opinion and begins to disprove Sue's belief. Both of them had been so caught up in their discussion that they almost didn't notice Principal Figgins and Emma walking in their direction.

"…I'm just saying that if you push her too much, she might fall off a cliff and that dentist would be there at the bottom to catch her — provided that he's wearing gloves, of course." Sue retaliates when Will says that he is going to do anything to win her back.

Emma looks at Will when she hears Sue say the word "dentist" and blushes. He wonders what she's thinking.

Figgins clears his throat. "William, Sue, I also need to have a word with you. Drop by my office in thirty minutes," he says and walks away with Emma. She still hasn't looked away from him and it bothers Will when he sees her palms close and open in anxiety.

When Figgins closes the door behind her, Emma breaks her silence. "If this is because of what I did — you know, shouting at you because you wanted to disband the Glee club, I am so sorry."

Figgins takes his seat behind the table. "This," he pauses. "is a more serious topic, Miss Pillsbury."

"How so?" Emma inquires.

"You are one of the educators here at McKinley to be laid off."


	2. Chapter 2

**A/N**: (**This chapter has been edited.**)

* * *

"Are you serious?" Emma asks, leaning forward in disbelief.

"The school board — observed every member of the faculty of this school and they deem that it isn't necessary to have a guidance counselor anymore since no one seems to drop by your office for counseling…except for William and his Glee kids."

"Oh that is absurd! Do you know how much my job actually means to me? How much I want to help not only the Glee Club but every single person in this school?" Her voice is painfully clipped and formal and Figgins gives her a look of sympathy. He knows how much she wants to help others despite not being able to help herself most of the time.

He was on her side, but he had no power over what was about to happen to Emma's career.

"Emma," Figgins begins to say, in a more casual tone. "this isn't permanent yet. They've given me a week to see this through. I can try to give a good word to the school board but I can't assure you that your name would be taken off the list."

"What should I do to keep my job? Should I give the students problems so that they would come to me?" Emma sighs frustratedly.

Figgins just stares at her, but he can't think of a word to say.

"I," Figgins is weighing his words carefully, she can tell. "I know you'll figure it out, Emma. You always do." He replies confidently and smiles at her.

Emma thanks him for his support and stands up to leave. Then, she sees Will and Sue talking in the receiving area and fakes a smile. Will eventually mouths "Is everything alright?" to her and she nods, proceeding to head back to her office.

* * *

Emma sat in her office, going over scheduling information and thinking of creating routine counseling sessions. A knock on her door, ever so quiet, pulls her from her thoughts. She entertains the thought of not bothering to acknowledge anyone who stands behind the door because at this moment, she would not be pleasurable company.

But there it is again, that soft, almost uncertain knock. Suddenly, an uneasy feeling settles in the pit of Emma's stomach, but before she's got any time to analyze the feeling, she has already unintentionally slammed the pen on her table and looked up from her paper. She sees Will with two cups of coffee in his slightly shaking hands, making an uncertain, timid impression.

She hasn't even let him yet, but he pushes the door with his side and enters her office.

"Now isn't a good time to talk, Will," Emma said, drifting her eyes back to the paper. "I'm busy. I'm…really busy."

"I heard about what happened; why Figgins called you. I just wanted to drop by and know if you're okay."

Her eyes glass over, voice trembling to a point where it nearly breaks. "Well, I'm not okay. I'm not okay at all. If you are about to get fired from the job that is keeping you together then you will not feel okay."

She notices that the cups of coffee are on a corner table now and he's just standing there, unmoving, only shuffling from one leg to the other, completely oblivious of the right things to be said.

"Damn it, Will. If you're just going to stand there, I'd rather have you leave than stare at me like that."

"Emma," Will starts, but obviously doesn't know how to continue, what to say. But that's alright, because she figures that she doesn't need him to talk, she just wants his presence there; it calms her down. He sits in his side of the table and Emma thinks he's about to tear up as well, but then he merely bends over the table, stretching out so he can get a hold of Emma's hands, dragging them back onto the table with his own.

"Why don't we look at the good side of this first? You can take a break from work…go to Hawaii…you always wanted to go there, right? Or you can focus on your relationship with Carl. You know, enjoy his company," he squeezed Emma's hands, his own eyes suddenly glassy yet voice firmly determined. "Everything's going to fall into the right place, Em."

"You don't know that," Emma utters desolately.

In fact, she was right; he didn't know. But he can hardly tell the woman currently breaking into pieces in front of him anything else.

They kept quiet for a moment, Will was trying to breathe through whatever his mind was guiding him to and she was on the verge of tears again.

"Maybe you can put up a sign that says, 'You can talk to me about anything'?" He says, then giving a small laugh.

"That is the craziest idea I have ever heard," Emma says petulantly. Will just shrugs.

"Sometimes, crazy works."


	3. Chapter 3

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	4. Chapter 4

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	5. Chapter 5

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	6. Chapter 6

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	7. Chapter 7

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	8. Chapter 8

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	9. Chapter 9

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	10. Chapter 10

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	11. Chapter 11

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	12. Chapter 12

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	13. Chapter 13

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	14. Chapter 14

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	15. Chapter 15

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	16. Chapter 16

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	17. Chapter 17

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	18. Chapter 18

**A/N**: (**The content of this chapter is to be edited by the author. I will update every chapter daily!**)


	19. Chapter 19

**A/N**: (**This chapter has yet to be published.) **I'm sorry for the misleading information (you know, receiving a notification from your email or whatsoever that I have updated this fic) but I really wanted to tell each and every one of my readers that I came back to finish this Will/Emma fanfic after three years of inactivity. I am also editing every chapter (the first one is already updated) to improve the horrendous writing I have committed.

Happy Holidays to all of you! -**youdalwayswin**


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